You will never believe this, but there was a time when Dennis Miller was actually funny. Now he just might be the least funny “comedian” on Twitter.

A few years ago, when Rolling Stoneranked all 145 Saturday Night Live cast members from best to worst, Miller came in at number 34, behind heavy-weights like Mike Myers, Tina Fey, and Will Ferrell (John Belushi topped the list), but ahead of current favorites Kate McKinnon and Kenan Thompson as well as comedic geniuses like Julia Louis-Dreyfus, Darrell Hammond, and most egregiously, Norm Macdonald.

“Let history record that when the Berlin Wall came down, Miller had the right cheap smirk at the right time, comparing the event to ‘Dean Martin and Jerry Lewis getting back together. I haven’t really enjoyed any of their previous collaborations, and I’m not sure I need to see their new stuff,’” Rolling Stone’s Rob Sheffield wrote of Miller’s six-year “Weekend Update” stint, from 1985 to 1991.

A year earlier, Vulture’s Dan Reilly named Miller the best “Weekend Update” anchor of all time, ahead of Macdonald, Fey, Amy Poehler, Seth Meyers, and everyone else who has held that job over the show’s four decades. He wrote that Miller “centered SNL every week through his satirical and passionate riffs on topics that favored cutting proclamations over one-liners” and posited that the show “has yet to find another anchor as versatile or essential as Miller proved to be.”

After leaving SNL, the comedian went on to HBO for the Emmy Award-winning, nine-season run of Dennis Miller Live, on which he further honed his hyper-literate political joke style, occasionally veering into self parody but still remaining firmly in the realm of comedy. Before John Oliver or Samantha Bee ever dreamed of “eviscerating” political foes, Miller would utter the words, “Now I don’t want to get off on a rant here,” as the screen went black behind him before unleashing his ire on some deserving target or another.

And yet, 16 years since that show was canceled, Miller has steadily devolved into just another right-wing blowhard—a disposition best personified by “Miller Time,” the regular segment he delivered on Fox News’ The O’Reilly Factor.

The tweet of Miller’s that got the most attention in recent weeks came the morning after Michelle Wolf’s controversial set at the White House Correspondents’ Dinner. After calling his fellow comedian a “horrid human being,” Miller said he would need some time to write some “brutally mean” jokes about her. Since when did this quick wit need three days to write a few jokes about someone?

In an interview last month, Miller tried to explain that his tweet about Wolf was meant to highlight the fact that he “had no idea who she is.” Apparently, the internet just didn’t “get it.”

After he was instantly mocked on Twitter for his bizarre promise (my favorite, from comedian Joe Randazzo: “Dennis Miller hasn’t written a funny joke since Daisy Fuentes tripped over a box of limited edition Slobodan Milošević Beanie Babies on the ‘Save the Whales’ episode of Supermarket Sweep”) Miller backed off, writing on Facebook that he would not be writing any “mean” jokes about Wolf. “I guess she just read the room,” he added.

Reading the room has seemingly become a challenge for Miller of late as he continues to try out terrible jokes on Twitter to no avail. Using the hashtag #DennisMillerOption to promote his new podcast, Miller tends to try out at least three or four jokes a day that all seem to lack the important ingredients of setup, punchline, and most of all humor.

For instance, there was this tweet just before last month’s royal wedding:

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Or how about this observation about the new Han Solo movie?

But of course, it is his attempt at conservative humor that really falls flat in Miller’s timeline.

And when Miller attempts the type of analogy-based joke construction that made him famous, it’s even worse.

Huh?

Wolf herself may have had the most perfectly succinct response to that particular joke when she tweeted one of Miller’s signature catchphrases back at him. With one word, the newest late-night host on the scene summed up just how irrelevant her wannabe critic has become.

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